Chlorosulfonamide salts, such as Chloramines T and M, have been extensively used as nitrogen sources in both asymmetric and racemic aminohydroxylations, aziridinations and allylic aminations (Bruncko et al. Angew. Chem., Int. Ed. Engl. 1996, 35, 454; Li et al. Angew. Chem., Int. Ed. Engl. 1996, 35, 451; Rubin et al. Angew. Chem., Int. Ed. Engl. 1997, 36, 2637). However, despite their effectiveness in those reactions, they have one common substantial drawback. The removal of the alkyl- or arylsulfonyl group from the introduced sulfonylamino group is often very problematic and requires extremely harsh conditions.
Recently, Weinreb and co-workers published a communication of a new protective group for amine: t-butylsulfonyl substituted amines were found to be stable under a variety of conditions, however the t-BuSO.sub.2 -group could be easily removed under relatively mild acidic conditions (sun et al. J. Org. Chem. 1997, 62, 8604). However, Weinreb did not prepare the chloramine salt of t-butylsulfonamide or demonstrate that it could be employed t as a nitrogen source in aminohydroxylation and aziridination of olefins.
What is needed is a readily accessable and effective nitrogen source of the type R--N.sup.(-) --Hal with an easily cleavable R--N bond which can be used in both catalytic aminohydroxylation and aziridination of olefins. Furthermore, what is needed is a simple and cost efficient method for producing such a nitrogen source.